Sodium Hydroxide → 2-(4'-Cyanobiphenyl-2-ylthio)-2-methylpropanoic acid

HRID 1503092Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][C:16]([CH3:23])([CH3:22])[C:17]([O:19]CC)=[O:18])=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+]>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15][C:16]([CH3:23])([CH3:22])[C:17]([OH:19])=[O:18])=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 2-(4′-cyanobiphenyl-2-ylthio)-2-methylpropanoate (93 mg, 0.286 mmol) and aqueous sodium hydroxide solution (1 M, 2 mL) in methanol (4 mL) was stirred at 60° C. for 12 hours. The reaction mixture was concentrated to remove methanol, acidified and filtered to obtain a white powder, which was purified by chromatography to yield 2-(4′-cyanobiphenyl-2-ylthio)-2-methylpropanoic acid (38.1 mg, 45%). By-product 2-(4′-carbamoylbiphenyl)-2-ylthio)-2-methylpropanoic acid (38.4 g) was also obtained. 1H NMR (400 MHz, DMSO-d6, 25° C.) 7.67-7.72 (m, 3H), 7.48-7.54 (m, 3H), 7.37-7.43 (m, 2H), 1.33 (s, 6H). MS (m/z) 296.16 (M-1).

Workup

concentrationThe reaction mixture was concentrated
customto remove methanol
filtrationfiltered
customto obtain a white powder, which
customwas purified by chromatography

Sources & evidence

ORD record: ord-5ec1deff4f20432bb55883e96886ac08
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212135B2

Reaction notes

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